ethyl (2E,4E,6E,8E,10E)-5,9-dimethyl-11-(2,6,6-trimethylcyclohexen-1-yl)-2,4,6,8,10-undecapentaenoate

Base Information

• Chemical Name: ethyl (2E,4E,6E,8E,10E)-5,9-dimethyl-11-(2,6,6-trimethylcyclohexen-1-yl)-2,4,6,8,10-undecapentaenoate
• CAS No.: 13979-19-6
• Molecular Formula: C₂₄H₃₄O₂
• Molecular Weight: 354.533
• Mol file: 13979-19-6.mol

Synonyms:ethyl (2E,4E,6E,8E,10E)-5,9-dimethyl-11-(2,6,6-trimethylcyclohexen-1-yl)-2,4,6,8,10-undecapentaenoate

Chemical Property of ethyl (2E,4E,6E,8E,10E)-5,9-dimethyl-11-(2,6,6-trimethylcyclohexen-1-yl)-2,4,6,8,10-undecapentaenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2E,4E,6E,8E,10E)-5,9-dimethyl-11-(2,6,6-trimethylcyclohexen-1-yl)-2,4,6,8,10-undecapentaenoate

There total 3 articles about ethyl (2E,4E,6E,8E,10E)-5,9-dimethyl-11-(2,6,6-trimethylcyclohexen-1-yl)-2,4,6,8,10-undecapentaenoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + all-trans-Retinal (116-31-4) → ethyl (2E,4E,6E,8E,10E)-5,9-dimethyl-11-(2,6,6-trimethylcyclohexen-1-yl)-2,4,6,8,10-undecapentaenoate (13979-19-6)

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 0.25h;

all-trans-Retinal; In tetrahydrofuran; at 0 - 20 ℃; diastereoselective reaction;

DOI:10.1248/cpb.c19-01005

Reference yield: 32.0%

(2E,4E)-ethyl hexa-2,4-dienoate (2396-84-1) + beta-carotene (7235-40-7) → C15H24 (1185252-35-0) + ethyl (2E,4E,6E)-5-methyl-7-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6-hepta-trienoate (74109-37-8) + ethyl all-E-13-demethylretinoate (60347-68-4) + ethyl (2E,4E,6E,8E,10E)-5,9-dimethyl-11-(2,6,6-trimethylcyclohexen-1-yl)-2,4,6,8,10-undecapentaenoate (13979-19-6)

Guidance literature:

With Hoveyda-Grubbs catalyst second generation; In toluene; at 20 ℃; for 72h; Inert atmosphere;

DOI:10.1016/j.tetlet.2009.06.032

Reference yield:

→ ethyl (2E,4E,6E,8E,10E)-5,9-dimethyl-11-(2,6,6-trimethylcyclohexen-1-yl)-2,4,6,8,10-undecapentaenoate (13979-19-6)

Guidance literature:

Carboxymethylentriphenylphosphonium-bromid, Retinal, Natriumethylat;

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

all-trans-Retinal

(2E,4E)-ethyl hexa-2,4-dienoate

beta-carotene

Downstream raw materials:

(2E,4E,6E,8E,10E)-5,9-dimethyl-11-(2,6,6-trimethylcyclohex-1-en-1-yl)undeca-2,4,6,8,10-pentaene-1-ol

β-apo-14'-carotenal

Refernces

• 1、 Wojtkielewicz, Agnieszka,Maj, Jadwiga,Morzycki, Jacek W.. "Cross metathesis of β-carotene with electron-deficient dienes. A direct route to retinoids". supporting information; experimental part. p. 4734 - 4737. Retrieved 2011/03/18.
• 2、 Blatz,Lin,Balasubramaniyan,Balasubramaniyan,Dewhurst. "A new series of synthetic visual pigments from cattle opsin and homologs of retinal.". . p. 5930 - 5931. Retrieved 2007/10/12.